The Battles of Fairfield and Monterey Pass

This entry is part 22 of 27 in the series The Gettysburg Campaign

The Battle of Fairfield took place concurrently with Pickett’s Charge on July 3, 1863. Maj. Gen. Alfred Pleasanton, the Union cavalry commander, ordered Brig. Gen. Wesley Merritt to depart from Emmitsburg with his brigade and strike the Confederate left and rear along Seminary Ridge.

Merritt was informed by a local that there was a Confederate supply train near the town of Fairfield, Pennsylvania. Merritt dispatched Major Samuel H. Starr with his 4 squadrons of the 6th US Cavalry to investigate and seize the wagon train.

Before they could get to the location, they were intercepted by the 7th Virginia Cavalry, leading a column under Confederate Brig. Gen. William E. “Grumble” Jones.

Jones’s Brigade had been raiding the Baltimore & Ohio Railroad in West Virginia and Maryland before being recalled by Lee. They hastened to Pennsylvania, crossing the Potomac River on July 1 (where Jones detached the 12th Virginia Cavalry to guard the ford) and camping at Chambersburg the following night.

Map of the Battle of FairfieldJones’s force had been reduced to the 6th7th, and 11th Virginia Cavalry and Preston Chew‘s Battery of horse artillery. Jones reached Fairfield on July 3 in response to Lee’s orders to secure the vital Hagerstown Road. They numbered about 1,050 troopers.

Starr dismounted his outnumbered force of 400 troopers and positioned them on a small ridge. Jones ordered a mounted charge that was repulsed. He then ordered his horse artillery to open fire on the Union force. After a bombardment, he ordered the 6th Virginia and the 7th Virginia to charge again. This time they overran the Union position. Starr’s force was pursued for three miles where a small number escaped through the Fairfield Gap.

The Battle of Fairfield was a disaster for the Union cavalry. Their losses were 6 killed, 28 wounded, and 208 unaccounted for, primarily prisoners. The losses for the Confederates were 8 killed, 21 wounded, and 5 missing.

Although Fairfield was a small engagement it was to have great importance on July 5th. Jones camped in the area and was able to hold the road open for the retreating Confederate army after their defeat at Gettysburg.

On July 4th, General George Meade, the Union commander, ordered his cavalry to strike the enemy’s rear and lines of communication so as to “harass and annoy him as much as possible in his retreat.” Eight of nine cavalry brigades took to the field. Col. J. Irvin Gregg‘s brigade moved toward Cashtown while all of the others moved south of Gettysburg. Brig. Gen. John Buford‘s division went directly from Westminster to Frederick, where they were joined by Merritt’s Reserve Brigade on the night of July 5.

Meade with his council of war determined that the Union infantry should remain at Gettysburg while the cavalry should pursue any Confederate retreat. Meade ordered Brig. Gen. Gouverneur K. Warren take a division from Maj. Gen. John Sedgwick‘s VI Corps and probe the Confederate positions.

Meade ordered preparations for a general movement of the army, which he organized into three wings, commanded by Sedgwick (I, III, and VI General William JonesCorps), Maj. Gen. Henry W. Slocum (II and XII), and Maj. Gen. Oliver O. Howard (V and XI). By the morning of July 5, Meade learned of Lee’s departure, but he hesitated to order a general pursuit until he had received the results of Warren’s reconnaissance.

The Battle of Monterey Pass, sometimes referred to as the Fight at Monterey Pass, began on the evening of July 4th between Union cavalry under Brig. Gen. Judson Kilpatrick and Confederate cavalry units commanded by Brig. Gens. Beverly H. Robertson and William E. “Grumble” Jones.

Lee’s withdrawal plan called for the wagon train of the wounded to take a longer route over the Chambersburg Pike, which passed through Cashtown in the direction of Chambersburg and Hagerstown, Maryland. The rest of his units were ordered to move through the South Mountain passes. They were to move along the Fairfield Road, through the Monterey Pass and there to Hagerstown, Maryland and south to Williamsport.

Maj. Gen. J.E.B. Stuart realized the importance of holding the mountain passes for the Confederate army to pass through. He assigned primary responsibility for this important task to the cavalry brigades of Robertson and Jones.

Meanwhile, Lt. Gen. Richard Ewell, who was in charge of the Confederate rear guard, realized the logistical challenge of moving through the passes. He sent his corps trains and herds of captured cattle ahead of his main body. He divided his wagons into three columns. The first used the Cashtown Gap, the second the Fairfield Gap, and the third the Monterey Pass.

The wagons headed for Monterey Pass followed the route of Maj. Gen. George Pickett‘s division (now reduced to brigade-size), which was moving to the rear as escorts for the Union prisoners of war from the battle.

Map of the Fight at Monterey PassMeanwhile, Kilpatrick, ever the aggressive cavalry commander, joined up with the brigade of Col. Pennock Huey at Emmitsburg, Maryland.   They were ordered to locate and destroy “a heavy train of wagons” that had been spotted by a Union signal station. Kilpatrick thought that this might be Lee’s main wagon train and  proceeded west on the Waynesboro-Emmitsburg Turnpike toward the village of Fountain Dale and Monterey Pass.

Click map to enlarge.

Stuart positioned Jones in the pass with his own 6th and 7th Virginia Cavalry regiments and a battery of horse artillery under Capt. Roger Preston Chew. The 7th Virginia was soon recalled, replaced by the 4th North Carolina Cavalry of Robertson’s Brigade.

The Union cavalry arrived at the pass on the evening of July 4th in a driving rainstorm. The Confederate guard unit at the top of the hill that led to the pass consisted of 20 cavalrymen under Captain George M. Emack from the 1st Maryland Cavalry Battalion, along with a single cannon. The 5th Michigan Cavalry immediately attacked the Confederate position but in the darkness did not realize how small a force they faced.

This small Confederate force was able to stall the Union advance long enough for reinforcements to arrive. While Jones sent forward reinforcements from the 6th Virginia, elements of his cavalry force attacked Huey’s brigade in the rear of Kilpatrick’s column.

After five hours of combat, the Union cavalry was able to seize the position and proceed to Monterey Pass. In a swirling battle, Union cavalry, led George Armstrong Custerby their daring commander Brig. Gen. George A. Custer attacked the Confederate wagon train in the darkness and rain. Custer was thrown from his horse and nearly captured. Grumble Jones also narrowly avoided capture.

More than 1,300 Confederates—primarily wounded men in ambulances, but also slaves, free blacks, and some cavalrymen, were captured and most of the wagons were destroyed. Union casualties were 43 (5 killed, 10 wounded, 28 missing).

Kilpatrick later reported that he had destroyed Ewell’s entire wagon train, although he had in fact encountered only a fraction of the full, 40-mile long train. The Confederates lost about 250 wagons and ambulances with casualties from Iverson’s and Daniel’s Brigades and of three artillery battalions, as well as 37 wagons from Maj. Gen. Robert E. Rodes’s division quartermaster trains.




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